Chloropyrazine → HCID 178479476, compound

HRID 1381497Notes

Reaction equation

HRID 1381497 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10]([NH2:14])=[C:9]([Cl:15])[N:8]=1)=[O:6].S(O)(O)(=O)=[O:17].CS[C:23](=[NH:25])[NH2:24].ClC1C=NC=CN=1.NC(=N)[OH:35]>O.CO>[OH2:6].[OH2:17].[OH2:35].[ClH:15].[NH:1]([CH2:2][CH2:3][NH:4][C:5]([C:7]1[C:12]([NH2:13])=[N:11][C:10]([NH2:14])=[C:9]([Cl:15])[N:8]=1)=[O:6])[C:23]([NH2:25])=[NH:24]

Participants

7

Reactant 4

HCID 73277ChloropyrazineHCID 752702-Methyl-2-thiopseudourea sulfateHCID 151481293,5-Diamino-N-(2-aminoethyl)-6-chloropyrazine-2-carboxamideHCID 178513210HCID 178513210, compound

Product 1

HCID 178479476HCID 178479476, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve the product of Step 1 (100 mg) and 2-methyl-2-thiopseudourea sulfate (122 mg) in water (0.5 ml) and MeOH (0.5 ml) and heat on a steam bath for 1 hour. If all the starting chloropyrazine is not reacted, add more pseudourea and repeat the procedure. Triturate the resulting residue in EtOH to obtain the sulfate salt of the title compound. Chromatograph the product on a high pressure reversed phase prep C18 column (Dynamax), eluting with MeOH:H2O (40:60), 0.2% TFA, at 10 ml/min., followed by a C18 Magnum 20 column (Whatman), eluting with MeOH:H2O (30:70), 0.2% TFA. Dissolve the resultant residue in 1N HCl, evaporate the solvent, redissolve in water and lyophilize to obtain the title compound as a yellow solid, m.p. 100° (d), M+ =272.

Workup

  1. temperatureheat on a steam bath for 1 hour
  2. customTriturate the resulting residue in EtOH

Sources & evidence

ORD record
ord-92d9c5d2a3cd4eca91a7dff6f9962d82
Source dataset
uspto-grants-1989_02
Patent number
US04803206

Reaction notes

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